Yarn treating process and composition therefor



Patented Jan. 9, 1940 YARN TREATING mocnss AND comosmon THEREFOR Joseph B. Dickey and James B. Normlngton, Rochester, N. Y assignors to Eastman Kodak Company, Rochester, N. Y.,-a corporation of New Jersey No Drawing. Application November 26, 1937,

' Serial No. 176397 v I 31 Claims. This invention relates to the conditioning 'of textile yarns and more particularly to the conditioning of filaments and yarns composed of organic derivatives of cellulose such as cellulose acetate, cellulose acetate'propionate, cellulose cellulose organic derivatives, it is necessary to.

treat the yarn in order to reduce thetendency toward breakage of the individual filaments or fibers when they are subjected to various me* chanical strains and to lubricate the yarn in order to facilitate handling in such operations as spinning, twisting, winding and reeling. In addition, it is necessary to treat yam to adapt it for use as warp or filling or for themanufactureof various types of knitted fabrics." In knitting, it is particularly important that the yarn be soft and pliable in order that it may conform readily to the contour of the needles, and thus produce a closely knitfabric free from "such defects as stitch distortion," pin holes,

laddeting, and the like.

Heretofore it has been proposed to employ softening agents such as .polyhydric alcohols and similar agentsas' ingredients of yarn conditiontaining them have certain drawbacks, one .of

, out at thesame time having too drastic a solvent action thereon. z

ingor lubricating formulas, generally in connection with'mineral, animal or vegetable. oils. It

has been found, however, that most of the known softening agents and'the various formulas conthe most serious ofwhich is high vapor pressure, and in some cases too drastic a solvent action on the yarn. Many of such agents pox sess slight or insumcient solvent power for the lubricants with which they are used, and it is ac cordingly necessary to employ blending agents or emulsifying agents in order to obtain operable yarn treating formulas. In addition, many of the known softening. and lubricating agents are insufliciently. soluble in water to permit satisfactory removal by ahueous scour baths.

This invention has as' its principalv object to provide an entirely new class of yarn conditioning agents which are particularly adapted for they treatment of yarns composed of orcontaining organic derivatives of cellulosev and capable of 7 lubricating, softeningand rendering such yarns more amenable to knitting, and other textile operations. A: furtherand specific object is to provide a class of conditioning agents which augment or assist the lubricating action of various lubricants when applied to such yarns. A'still further object is to provide, yarn softening and lubricating formulas which can be readily re-- moved from the yarns by the usual scour baths. A still further object is-to provide an improved -method-for the conditioning of yarns, particularly those composed of or containing organic derivatives of cellulose such'as cellulose acetate, ,whereby the yarn is rendered soft and pliable and capable of employment in a variety of textile operations where complicated designs orv stitches are employed. Another object is to provide an improved type .or yarn which is especially amenable to textile operations including knitting, weaving, spinning and the like. Still another object is to provide new chemical compounds having the structure-and properties discussed below. Other objects will appear hereinafter.

, These objects are accomplished by. the following invention which, in its broader aspects, comprises the discovery that acetalshaving the general formula: I v 01c BO -OHr-C\ it on where It is an"aikoxyalkyl, aryloxyalkyl or heterocyclic group, R' is an alkyl group'such as methyl,ethyl, propyl, etc.,may be usedas yarn conditioning agents and: particularly as softening agents, with 'or' without the addition of animal,

mineral, or vegetable oils, in the treatment of yarns composed of or containing organic derive ing. action on cellulose organic derivative yarns which-renders such yarns soft and pliable with- I z,1 8,6,63o- ATENT OFFICE The above compounds may be prepared fromv halogenated acetals prepared in accordance with the method described 1111.1. A. c. s., v01. 49, page 2517 (1927) and annalen, Vol. 279, page 300.,

-- Typicalexamples of compounds of this type p-ethoxy-p-ethoxyethoxydiethylal 138-14571? p'butoxy- 3-ethoxyethoxydiethylal 148-15 O/ 15 Tetrahydrofurfuryloxydiethylal 120-1247 15 fi-methoxyethoxydimethylal- '71- '79/ 12 fl-ethoxyethoxydimethylal 86- 90/'12 fl-butoxyethoxydimethylal 112-1 16 15 fl-ethoxy-p4ethoxydimethylal 130135/ 15 p'-butoxy-fl-'ethoxydimethylal 153-158/l5 Tetrahydrofurfuryloxydimethylal 105111/ 8 As illustrating the preparation of these compounds two examples of the preparation'of typical below:

- Millimeters p-methoxy. ethoxydiethylal 86- 92/ 15 fl-ethoxyethoxydiethyl'al -100/16-- Pmmnon or p-mnoxmaommnm Twenty-three grams of sodium are dissolved in 180'grams of ethylene glycolmonomethyl ether.

. To this mixture, heated to 100, are added 153 grams of chlorodiethylal. When the addition is complete, the reaction mixture is refluxed for ten-hours. The salt is then separated, and the reaction product is obtained by distillation. An-

excellent yield of fl-methoxyethoxydiethylal boil:- ing at 86-92/15 mm. is obtained. A catalyst such as copper oxide, copper acetate, copper powder, etc., may be used.

Pmxm'non or Tsraxnrnaoroarusmxrmmnmr.

P Fifty-six grams of potassium hydroxide are dissolved in 500 cc. of tetrahydrofurfuryl alcohol. To this mixture, heated to 50, are added dropwise with stirring 125 grams of chlorodimethylal. The reaction is finished by heating to 100-125". The salt is removed by filtration and the reaction products fractionated. Tetrahydrofurfuryloxydimethylal with a boiling point of 105-111 /8 mm. is obtained. COPper'oxide, copper acetate, copper powder, etc., or any suitable basic halogen acid removing agent, may be used as a catalyst.

In accordance with the invention these compounds may be applied directly .to the yarn during or after spinning, or may be added to the spinning solution itself. We have found that these compounds-have exceptional solvent powers which enable them to dissolve mineral oils and blown and unblown, drying and semi-drying, vegetable and animal oils and accordingly they may be, and preferably are, employed ,as ingredients of yarn conditioning or lubricating formulas in conjunction with agents which function wholly or partially as lubricants.

In the following examples and description we have set forth several of the preferred emboditypical applications of the invention are set forth:

- Example I A 20% solution of cellulose acetate in acetone in which is incorporated 1-25% by weight of the cellulose acetate of p'-butoxy-p -ethoxydiethyla1 is extruded through orifices into an evaporative atmosphere. The filaments thus produced are wound, or twisted and wound. Yarns produced from filaments thus prepared are pliable and suitable for knitting.

Eramme II Yarn designed for knitting and composed of cellulose acetate is treated by applying thereto tetrahydrofurfuryloxydipropylal by means of an applicator roll. The amount of the conditioning liquid applied may run from 4 to 25% by weight of the untreated yarn. If the yarn is intended for weaving, the same procedure may be followed,

except that the amount of conditioning liquid added to the yam is' only about 1 to 5%.

' Example In A conditioning liquid is made up by mixing the following ingredients in the indicated proportions:

' Percent p-methoxyethoxydibutylai I "I Oliveoil Q 30 This composition is applied to a cellulose acetate yarn intended for knitting in an amount repre-f senting 4 to 25% by weight of the untreated yarn. The filaments or fibers treated as described 7 above are'quite soft and pliable and give excellent results in textile operations, especially in knit-- t g Example Ill Example V Yarn designedfor knitting and composed of cellulose acetate is treatedby applying, thereto tetrahydrofurfuryloxydiethyla1 by means of an applicator roll. The amount of the conditioning liquid applied may run from 4 to 25% by weight of the untreated yarn. If the yarn is intended for weaving, the same'procedure may be followed, except that the amount of conditioning liquid' added to the yarn is only about 1 to Example VI a A 20% solution of cellulose acetate in acetone in which is incorporated 1-25% by weight of the cellulose acetate of p'-ethoxy-fl-ethoxydimethylal is extruded through orifices into an evaporativeatmosphere. The filaments thus produced are wound, or twisted and wound. Yarns produced from filaments thusprepared are pliable and suitable for knitting,

Other examples ofyarn conditioning compositions which may be applied to various types of yarn, particularly those composed of or contain- '40 ing cellulose acetate, cellulose acetate propionate,

cellulose acetate butyrate, and similar cellulose organic acid esters, in accordance with our inven- I tion, and which render such yarns soft and pliable and especially well adapted for various texv tile operations, particularly knitting, are the following:

- Example VII I Percent s-methaxyethoxydiethyilal 60 Blown olive oil I v 40 Example VIII Percent p-ethoxyethoxydiethylalu -70 Neats-foot oil i 30 Example IX i Percent p-butoxyethoxydiethylaL", 70 Light mineral il 30 .E'zdmple X Percent p'-ethoxy-p-etltoiwethoxydiethylal 70 Blown neat's-foot oil 30 Example x1 Percent ,s-tetrahydrofurfuryloxydiethylal 70 Sperm. oil a 30 *Ezample XII Tetrahydrofurfuryloxydimthyhl 2o Gelatin 10' Water Sulfonated castor 'oiL...-. ..'..........-r........- s u Emample XIII Per cent Water soluble cellulose ester Water I 80 p'-butyoxy-p-ethoxyethoxydimethylal 10 As will be apparent from'the above examples and description, the conditioning agents of our invention may be applied by a wide variety of methods. For example, we may employ the agent as an ingredient of the spinning dope from which the filaments are formed, the amount of the agent so employed depending upon a number of 7 factors, such as the particular cellulose derivative used in making the yarn, the solvent or sol-' vent combination used in making up the spinning solution, and the degree of softness or pliability desired in the yarn, etc.

If the conditioning agent is to be applied to the yarn after spinning, this may be done by bringing the yarn in contact with a wick, roll,

, or felt wet therewith or the liquid may be applied by immersion, spray, or otherwise. The

particular point at which the liquid is applied may vary. It may, for example, be applied to the yarn inside or outside the spinning cabinet, be-

tween the guide and godet roll, between the godet or other roll or guide and the point of winding and/or twisting. In some cases, the liquid may even be applied to' the yarn'after winding onto cones, spools, bobbins, or the like or by the so-called bobbin to bobbin method. In the case of staple fiber manufacture, the liquidmaybe applied to the yarn prior to', or after cutting into staple lengths. I

The amount of the agent so employed will vary widely dependin upon the results desired, the specific nature of the material to which the agent is applied, the use to which the yarn is eventually to be put and other factors. For example, in

a given casewhere acellulose organic acid ester yarn such as a yarn composed of cellulose acetate, is intended for knitting, about 4 to 25% or more by weight, based on the weight of the dry yarn, may-be satisfactory, while if the yarn is intended for weaving, the amount may varybetween about 1 and 5%.

Although in the above examples we have referred primarily to yarn treating compositions "the composition is intended. For example, ifit.

containing only the conditioning agent and an all, other ingredients such as solvents, non-sol vents, emulsifying agents, blending agents and the like, may be added within the scope of our invention, Likewise, various dyes or other coloring matter may be'included in case his desired to permanently or fugitively tint or dye the ma- 5 terial undergoing treatment. Although we have found it convenient to illustrate our invention byreference to compositions containing specific percentages ofthe various in-' gredients, these percentages may vary widely depending upon the particular purpose for-which is desired to'controlvthe solvent or softening action of the conditioning agent, the amount of the agent may be adjusted as, for example by reducing the amount of the a ent and correspondingly increasing the amount of oil or other ingredient.

Whilewe have described our invention with particular reference vto the treatment of yarns composed of organic derivatives of cellulose such as cellulose acetate, the conditioning agents and formulas described herein are'applicable-to the conditioning of many other types of cellulose derivative yarns such as those composed of or containing cellulose propionate. cellulose butyrate,

cellulose acetate propionate, cellulose acetate butyrate, ethyl cellulose, methyl cellulose, benzyl cellulose and others', as well as to the conditioning of silk, wool, cotton, viscose and other natural or artificial materials.

The term yarn as used herein and in the claims is to be understood as including a single filament, a plurality of filaments associated into together, composite threads composed of a mixture of natural and artificial filaments or a composite thread formed by twisting together individual strands of natural or artificial materials, as well as cut staple fibers'produced from natural and/or artificial filaments or threads and spun yarn produced from such staple fibers.

the form of a thread, either of high or low twist, "single or multiple threads associated or twisted As indicated above, the yarn conditioning agents of. our invention are exceptionally good solvents for a wide variety of mineral, blown and characteristic of the agents employed in accordance with the invention is their ability to soften yarns, especially those composed of or containing organic derivatives of cellulose such as cellulose I acetate andrender them soft and pliable and amenable-to various textile operations, especially operations such as those involved in weaving and knitting where complicated designs or stitches are employed, without too drastic an action on the yarn material. Another outstanding characteristico'fthese compounds'is their exceptional sol- \40 vent power-for a wide variety of mineral, animal and vegetable oils and their ability to act as lubricating assistants in conjunction with these oils when applied to such yarns. In addition, due to their solubilityin water, they may be readily removed from yarns and fabrics in means of the usual aqueous-scour baths. By, employing the yarn conditioningagents and method of our inf'vention ashereln described. one 'is enabled-to obtain highly satisfactory results in the manufacture of-yarns and woven fabrics and especially the production from these yarns of closely knit fabrics free from defects such as pin holes,

' stitch distortion, laddering and the like.

What we claim and desireto secure by Letters Patent of the United States is:

1. The process of conditioning yarn to render it more amenable to textile operations including knitting, weaving, spinning and the like which Scomprises applying thereto a lubricating and softening'composition containing as its essential lubricating and softening component an:

acetal having the eneralformula:

Re-O-KifirC I where R is an organic 'radicalselected fromthe I .group consisting 'of alkoxyalkyl, aryloxiirallryl,

and heterocyclic groups, andR' is an alkyl group. 2; The process of conditioning yam composed of orcontaining organic derivativesof'cellulose to render it more amenable to textile operations including knitting, weaving, spinning and thev like. which'compris'es applying thereto a lubricating and softening composition containing as its essential lubricating and softening compound an acetal having the general formula:

where B. is an organic radical selected from the group consisting of alkoxyalkyl, aryloxyalkyl,

and heterocyclic groups, and R. is an alkyl group.

i 3. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component an acetal having the general formula:

R-O-CHr-C wnere R is an organic radical selected from the group consisting of alkoxyalkyl, aryloxyalkyl and heterocyclic groups, and R is an alkyl group, and a textile lubricant.

The processof conditioning yarn to render it more amenable to textile operations including knitting, weaving, spinning and the like which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softeningcomponent an acetal having the general formula:

where R is an alkoxyalkyl, and R. is an alkyl group of the class propyl, etc.

6. The process of conditioning yarn to render it more amenable to textile operations including knitting, weaving, spinning and the like which 0 comprises applying thereto a lubricating and.

softening composition containing as its essential lubricating and softening component an acetal having the general formula:

. on lit-O-CHr-U K OR! I where R is an aryloxyalkyl group, and R. is an 'alkyl group of the class consisting 'of methyl,

70 ethyl, propyl, etc. a

'2. The process of conditioning yarn to render it more amenableto textile operations including knitting, weaving,,spinning and the like which comprises applying thereto alubricating and .75 softening composition containing as its essentialconsisting of 7 methyl, ethyl,

lubricating and softeningicomponent an acetal having the general formula:'

0 a Ro-cmo where R is a heterocyclic group, and R. is an-alkyl group of the class consisting of methyl, ethyl, propyl, etc.

8. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to-textile operations including knitting, weaving, spinning, and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component p'-butoxy- ,c-ethoxyethoxydiethylal.

'9. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile-operations including knitting,-weaving, spinning, and the like, which comprises applying thereto a lubricating and softeningcomposition containing as its essential lubricating and softening component tetrahydrofurfuryloxydie'thyial. I

10. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the-like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component pf-ethoxy-p-ethoxydimethy1a1.

11. A conditioning agent for rendering yarns more amenable to textile operations including knitting, weaving, spinning, and the like, which comprises an acetal having the general formula:

where R is an organic radical selected from the group consisting of alkoxyalkyl, aryloxyalkyl, and heterocyclic groups, and R is an alkyl group.

12. A conditioning agent for rendering textile yarns composed of or containingorganic derivatives of cellulose more amenable to textile operations including knitting, weaving, spinning and the like, which comprises an acetal having the general formula:

, 0R. n-o-onf-o on where R is an organic radical selected from the group consisting of alk'oxyalkyl, aryloxyalkyl and heterocyclic groups, and R is an alkyl group,

and a textile lubricant.

13. A conditioning agent for rendering yarns more amenable to textile operations including knitting, weaving, spinning and the like, which comprises an acetal having the general formula:

n-o-on=o where R is an alkoxyalkyl group and R is an alkyl group of the class consisting of methyl,

ethyl, propyl, etc.

14. A conditioning agent for rendering yarns more amenable to textile operations including knitting, weaving, spinning, and the like, which comprises an acetal having the general formula:

R-Mm-O 5 a Pom where R is an aryloxyalkyl group. and R is an alkyl group of the class consisting of methyl, ethyl, propyl, etc.

15. A conditioning age'ntior rendering yarns more amenable to textile operations including knitting, weaving, spinning, and the like, which comprises an acetal having the general formula:

on where B is a heterocyclicgroup, and R is an alkyl group of the class consisting of methyl, ethyl, 0 propyl, etc.

16. A conditioning agent for rendering yarns composed of or containing a cellulose acetate ,"more amenable to textile'operations including knitting, weavins, spinning, and the like con- 2 taining p'-butoxy-p-ethoxyethoxydiethylal.-

1'7. A conditioning agent for rendering textile .yarns composed of or containing cellulose acetate more amenable to textile operations including knitting, weaving, spinning, and the like, con- 30 taining tetrahydroiurfuryloxydiethylal. 18. A conditioning agent for rendering textile yarns composed of or containing cellulose acetate more amenable to textile operations including knitting, weaving, spinning and the like con- 86 tainlng p'-ethoxy-p-ethoxydlmethylal.

' l9.-Textile yarn amenable to textile opera tions including knitting, weaving. spinning, and the like impregnated with a lubricant containing an acetal having the general formula: 40 on B-(l-OHs-O 9012. v where R is anorganic radical selected from the 45 group consisting oi! alkoxyalkyl, arylonalkyl,

and heterocyclic grqups. and R'is an alkyl group.

20. Textile v yarn composed of or containing organic derivatives of cellulose amenable to textile operations including knitting, wee-vim. spinso ning, and the like, impregnated with a conditioning agent comprising an acetal having the general iormula: I oa' n o a! p where R is an'organic radical selected from the group of alkoxyalhl, aryloxyalkyl, and heterocyclic groups, and R is an albl group.

. 21. Textile yarn'composed of or containing organic derivatives of cellulose amenable to textile operations including knitting, weaving. spinning,andtbelike,tedwithaoonditioningagentcomprilinganacetllhavingtbegenu 'eral-iornmla:

m oi alboxnlhl. arylonalhl WmandR'-ilanalkflgroop, andatoxtile'lubricanai 2am yarn amenable to textile operam'mmIQ mam'M- mar-ethos,-

the like impregnated with a lubricant containing an acetal the general formula:

24. Textile yarn amenable to textile opera- .tions including knitting, weaving, spinning, and

the like impregnated with a lubricant containing anacetal having the general formula:

. oa' n-o-oHi-0 V where R is a heterocyclic group, and It is an alkyl group.

25. Textile yarns composed of or containing cellulose acetate amenable to textile operations 1 including knitting, weaving, spinning and the like, impregnated with a lubricant comprising p' butoxy-p-ethoxyethoxydiethylal. 26. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning, and the like, impregnated with a lubricant comprising tetrahydroiurmryloxydiethylal. 2'7. Textile yarns composed of or containing cellulose acetate amenable to textile operations 40 including knitting, weaving, spinning, and the like, impregnated with a lubricant comprising p'-ethoxy-p-ethoxydimethylal.

28. As new chemical compounds, aoetals having the general iormula:

.where R is an organic radical selected from the group consisting of alkoxyalkyl, arylonaikyl,

and heterocyclic groups, and R is an alkyl group.

29. Asa new chemical compound, p'-butoayp-ethoxyethoxydiethylal having the structural Iormula: I s v oar-o-osreoc m-o-o so. Asanew chemical compound,tetrahydroso wuryloxydiethylal having the structural torm- O s-0E1 coin.

- on-oWnr-ofi o ooim snsnnewenunieu' oom oanna. moms.

June a. a.

3'". fro 

